US4524014A - Photobleach system, composition and process - Google Patents

Photobleach system, composition and process Download PDF

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Publication number
US4524014A
US4524014A US06/467,545 US46754583A US4524014A US 4524014 A US4524014 A US 4524014A US 46754583 A US46754583 A US 46754583A US 4524014 A US4524014 A US 4524014A
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Prior art keywords
acceptor
donor
chromophore
electron
alpcs
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Expired - Fee Related
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US06/467,545
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English (en)
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Timothy D. Finch
Stuart W. Beavan
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Lever Brothers Co
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Lever Brothers Co
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3932—Inorganic compounds or complexes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/0063—Photo- activating compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/50—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs by irradiation or ozonisation

Definitions

  • This invention relates to improved photobleach systems and to compositions comprising said system.
  • Photobleaches are known in the art. Generally photobleaches exert their bleaching action from the production of a reactive oxidising species through photochemical activation by absorption of visible and/or ultraviolet radiation. Examples of photobleaches are porphine compounds, particularly phthalocyanines and naphthalocyanines, described in the literature as photoactivators, photochemical activators or photosensitizers.
  • Preferred electron donors are those which on transferring its electron will not be capable of undergoing the reverse reaction.
  • "sacrificial" electron donors are usable for the present invention.
  • the reducing power necessary for the electron donor will obviously depend on the nature of the excited acceptor in question, i.e. on thermodynamic grounds there is an interdependency between the reduction potentials of the donor and the acceptor in its excited state and electron donors with reduction potential E° lower than the reduction potential of reaction (2) will reduce.
  • Suitable chromophore acceptors are those having a reduction potential E° (acceptor/acceptor ) ⁇ 0.0 eV., preferably ⁇ -0.4 eV. and E° (acceptor*/acceptor ) ⁇ 3.0 eV., preferably ⁇ 0.8 eV.
  • Suitable electron donors are those having a reduction potential E° (Donor + /Donor) ⁇ 3.0 eV., preferably ⁇ 0.8 eV.,
  • porphine photoactivators fall under the above definition and will be suitable for use as the chromophore acceptor in the present invention.
  • the photobleach system of the invention is preferably used in or with a detergent composition, particularly for washing and/or treating fabrics, including fabric softening compositions.
  • the photobleach system of the invention can be incorporated in solid detergent compositions which may be in the form of bars, powders, flakes or granules, but is also especially suitable for use in liquid detergent compositions both built and unbuilt.
  • a photobleach system comprising a porphine photoactivator and an alkali metal sulphite is used.
  • Solid powdered or granular formulations embodying the system/compositions of the invention may be formed by any of the conventional techniques e.g. by slurrying the individual components in water and spray-drying the resultant mixture, or by pan or drum granulation of the components, or by simply dry mixing the individual components.
  • Liquid detergents embodying the system/compositions of the invention may be formulated as dilute or concentrated aqueous solutions or as emulsions or suspensions.
  • Liquid detergents comprising a photobleach system of the invention may have a pH ranging from 8-11, preferably ⁇ 10, particularly ⁇ 9, and should preferably be packed in opaque containers impervious to light.
  • the invention also includes detergent compositions comprising an organic detergent compound, a chromophore acceptor as defined hereinbefore and an electron donor as defined hereinbefore.
  • the chromophore acceptor may be present therein in a proportion of about 0.001 to about 10% by weight of the composition and the electron donor in a proportion of from about 1 to 40% by weight of the composition.
  • Preferred usage of chromophore acceptor in a detergent composition is from 0.001 to 2%, particularly in the lower range of between 0.001 and 0.1% by weight of the composition.
  • organic detergent compound i.e. surfactant, which may be anionic, nonionic, zwitterionic or cationic in nature or mixtures thereof in the compositions of the invention are preferably those conventionally used and may be from about 2 to 60% by weight.
  • anionic non-soap surfactants are water-soluble salts of alkyl sulphate, paraffin sulphonate, alpha-olefin sulphonate, alpha-sulfocarboxylates and their esters, alkyl glyceryl ether sulphonate, fatty acid monoglyceride sulphates and sulphonates, alkyl phenol polyethoxy ether sulphate, 2-acyloxy-alkane-1-sulphonate, and beta-alkyloxy alkane sulphonate. Soaps are also preferred anionic surfactants.
  • alkyl benzene sulphonates with about 9 to about 15 carbon atoms in a linear or branched alkyl chain, more especially about 11 to about 13 carbon atoms; alkyl sulphates with about 8 to about 22 carbon atoms in the alkyl chain, more especially from about 12 to about 18 carbon atoms; alkyl polyethoxy ether sulphates with about, 10 to about 18 carbon atoms in the alkyl chain and an average af about 1 to about 12 --CH 2 CH 2 O--groups per molecule, especially about 10 to about 16 carbon atoms in the alkyl chain and an average of about 1 to about 6 --CH 2 CH 2 O--groups per molecule; linear paraffin sulphonates with about 8 to about 24 carbon atoms, more especially from about 14 to about 18 atoms; and alpha-olefin sulphonates with about 10 to about 24 carbon atoms, more especially about 14 to about 16 carbon atoms; and soaps having from 8
  • Water-solubility can be achieved by using alkali metal, ammonium, or alkanolamine cations; sodium is preferred. Magnesium and calcium cations may also be used under certain circumstances e.g. as described by Belgian Pat. No. 843,636.
  • anionic surfactants such as a mixture comprising alkyl benzene sulphonate having 11 to 13 carbon atoms in the alkyl group and alkyl polyethoxy alcohol sulphonate having 10 to 16 carbon atoms in the alkyl group and an average degree of ethoxylation of 1 to 6, may also be used as desired.
  • nonionic surfactants are water-soluble compounds produced by the condensation of ethylene oxide with a hydrophobic compound such as an alcohol, alkyl phenol, polypropoxy glycol, or polypropoxy ethylene diamine.
  • Especially preferred polyethoxy alcohols are the condensation products of 1 to 30 moles of ethylene oxide with 1 mol of branched or straight chain, primary or secondary aliphatic alcohol having from about 8 to about 22 carbon atoms; more especially 1 to 6 moles of ethylene oxide condensed with 1 mol of straight or branched chain, primary or secondary aliphatic alcohol having from about 10 to about 16 carbon atoms; certain species of polyethoxy alcohol are commercially available under the trade-name "Neodol®", “Synperonic®” and "Tergitol®”.
  • Preferred examples of zwitterionic surfactants are water-soluble derivatives of aliphatic quaternary ammonium, phosphonium and sulphonium cationic compounds in which the aliphatic moieties can be straight or branched, and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic water-solubilizing group, especially alkyl-dimethylpropane-sulphonates and alkyl-dimethyl-ammonio-hydroxypropane-sulphonates wherein the alkyl group in both types contains from about 1 to 18 carbon atoms.
  • cationic surface active agents include the quaternary ammonium compounds, e.g. cetyl trimethyl ammonium bromide or chloride; and distearyldimethyl ammonium chloride; and the fatty alkyl amines, e.g. di-C 8 -C 26 alkyl tertiary amines and mono C 10 -C 20 alkyl amines.
  • compositions may also contain an (alkaline) detergency builder.
  • an (alkaline) detergency builder for example conventional (alkaline) detercency builders, inorganic or organic, can be used at levels up to about 80% by weight of the composition, preferably from 10% to 60%, especially from 20% to 40% by weight.
  • Suitable inorganic alkaline detergency builders are water-soluble alkalimetal phosphates, polyphosphates, borates, silicates and also carbonates.
  • Specific examples of such salts are sodium and potassium triphosphates, pyrophosphates, orthophosphates, hexametaphosphates, tetraborates, silicates and carbonates.
  • Suitable organic alkaline detergency builder salts are: (1) water-soluble aminopolycarboxylates, e.g. sodium and potassium ethylenediaminetetraacetates, nitrilotriacetates and N-(2-hydroxyethyl)-nitrilodiacetates; (2) water-soluble salts of phytic acid, e.g. sodium and potassium phytates (see U.S. Pat. No.
  • water-soluble polyphosphonates including specifically, sodium, potassium and lithium salts of ethane-1-hydroxy-1,1-diphosphonic acid; sodium, potassium and lithium salts of methylene diphosphonic acid; and sodium, potassium and lithium salts of ethane-1,1,2-triphosphonic acid.
  • zeolites or aluminosilicates can also be used.
  • One such aluminosilicate which is useful in the compositions of the invention is an amorphous water-insoluble hydrated compound of the formula Na x (xAlO 2 .SiO 2 ), wherein x is a number from 1.0 to 1.2 said amorphous material being further characterized by a Mg ++ exchange capacity from about 50 mg eq. CaCO 3 /g. to about 150 mg eq. CaCO 3 /g. and a particle diameter of from about 0.01 micron to about 5 microns.
  • This ion exchange builder is is more fully described in British Pat. No. 1,470,250.
  • soil-suspending agents for example sodium carboxymethylcellulose; optical brightening agents; lather control agents; dyes; perfumes; enzymes, particularly proteolytic enzymes and/or amylolytic enzymes; and germicides may also be included.
  • the substrate or the bleach liquor must be irradiated with radiation capable of absorption by the chromophore/acceptor which can range from the near ultra-violet (i.e. ⁇ 250 nm) through the visible spectrum to the near infra red (i.e. ⁇ 900 nm).
  • radiation capable of absorption by the chromophore/acceptor which can range from the near ultra-violet (i.e. ⁇ 250 nm) through the visible spectrum to the near infra red (i.e. ⁇ 900 nm).
  • this radiation must include light of wavelength 600-700 nm. Suitable sources of light are sunlight, normal daylight or light from an incandescent or fluorescent electric lamp bulb.
  • the intensity of illumination required depends on the duration of the treatment and may vary from the normal domestic lighting in the case of several hours soaking, to the intensity obtained from an electric light mounted within a short distance of the surface of the treatment bath in a bleaching and/or washing process.
  • the concentration of chromophore acceptor in the washing and/or bleaching solutions can be from 0.02 to 500 parts per million, preferably from 0.1 to 125 ppm, particularly from 0.25 to 50 ppm.
  • the concentration of electron donor required in the washing and/or bleaching solution should be at least 3 ⁇ 10 -5 M, preferably ⁇ 5 ⁇ 10 -4 M and particularly within the range of between 5 ⁇ 10 -3 M and 2 ⁇ 10 -2 M.
  • FIG. 1 shows a plot of the photobleaching of a direct red dye Direct Fast Red 5B (DR81) in alkaline aqueous solution, buffered with sodium triphosphate to pH 9.8, by AlPCS as a function of cysteine concentration.
  • DR81 Direct Fast Red 5B
  • FIG. 2 shows a plot of the reduction in DR81 concentration against radiation time for thiosulphate alone, AlPCS alone and AlCPS/thiosulphate.
  • the dye DR80 is completely photostable in the presence of Na 2 SO 3 alone and the mixture is thus again highly synergistic.
  • FIG. 2 the reduction in DR81 concentration is set out against radiation time for thiosulphate alone, AlPCS alone and ALPCS/thiosulphate. The enhancement achieved with the ALPCS/thiosulphate system is evident.
  • Pre-washed EMPA 114 clothes were soaked in sodium triphosphate (STP) buffered solutions of AlPCS. The fabrics were then irradiated for 90 minutes with simulated solar radiation. During this irradiation the clothes were rewetted with either Na 2 SO 3 solution (0.5, 1.0 and 2.0 g/l) or STP solution of identical pH every 30 minutes. The monitors were rinsed, dried and the bleaching obtained measured by monitoring the change of reflectance at 460 nm ( ⁇ R 460 ). Various levels of adsorbed AlPCS were investigated, but as an example one such level achieved by a 20 min soak has been selected to show the synergistic effects possible.
  • STP sodium triphosphate

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US06/467,545 1982-02-19 1983-02-17 Photobleach system, composition and process Expired - Fee Related US4524014A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB8204959 1982-02-19
GB8204959 1982-02-19
GB8206842 1982-03-09
GB8206842 1982-03-09

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US4524014A true US4524014A (en) 1985-06-18

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US (1) US4524014A (en))
EP (1) EP0087833B1 (en))
AU (1) AU544554B2 (en))
BR (1) BR8300801A (en))
CA (1) CA1202452A (en))
DE (1) DE3364300D1 (en))
ES (1) ES519881A0 (en))
GB (1) GB2115027B (en))
GR (1) GR78065B (en))
IN (1) IN156753B (en))
MY (1) MY8700476A (en))
NO (1) NO830577L (en))
PT (1) PT76256B (en))

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3729474A1 (de) * 1986-09-08 1988-03-10 Colgate Palmolive Co Zusammensetzung zum behandeln und reinigen von textilien
US5972038A (en) * 1994-08-30 1999-10-26 The Procter & Gamble Company Chelant enhanced photobleaching
US6413924B2 (en) * 1997-01-24 2002-07-02 Case Western Reserve University Photobleaching compositions comprising mixed metallocyanines
US8568991B2 (en) 2011-12-23 2013-10-29 General Electric Company Photoactivated chemical bleaching of dyes
US9176032B2 (en) 2011-12-23 2015-11-03 General Electric Company Methods of analyzing an H and E stained biological sample
US9464375B2 (en) 2014-01-24 2016-10-11 The Procter & Gamble Company Kit for treating a substrate
JP2017506272A (ja) * 2014-01-24 2017-03-02 ザ プロクター アンド ギャンブル カンパニー 表面を処理するためのシステム及び方法
US9834740B2 (en) 2014-01-24 2017-12-05 The Procter & Gamble Company Photoactivators
US9915592B2 (en) 2013-03-06 2018-03-13 General Electric Company Methods of analyzing an H and E stained biological sample
US10098519B2 (en) 2014-01-24 2018-10-16 The Procter & Gamble Company Lighted dispenser
US10111574B2 (en) 2014-01-24 2018-10-30 The Procter & Gamble Company Method for treating dishware
US12139840B2 (en) 2018-06-11 2024-11-12 The Procter & Gamble Company Photoactivating device for washing machine

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8900807D0 (en) * 1989-01-14 1989-03-08 British Petroleum Co Plc Bleach compositions
US5376288A (en) * 1989-06-21 1994-12-27 Noro Nordisk A/S Detergent additive granulate and detergent
DK306289D0 (da) * 1989-06-21 1989-06-21 Novo Nordisk As Detergentadditiv i granulatform
WO1997031994A1 (en) * 1996-03-01 1997-09-04 The Procter & Gamble Company Chelant enhanced photobleaching
US20150210964A1 (en) * 2014-01-24 2015-07-30 The Procter & Gamble Company Consumer Product Compositions

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1372035A (en) * 1971-05-12 1974-10-30 Procter & Gamble Ltd Bleaching process
US3927967A (en) * 1972-06-02 1975-12-23 Procter & Gamble Photoactivated bleaching process and composition
US4033718A (en) * 1973-11-27 1977-07-05 The Procter & Gamble Company Photoactivated bleaching process
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
US4094806A (en) * 1975-04-03 1978-06-13 The Procter & Gamble Company Photoactivated bleach-compositions
EP0003149A2 (en) * 1978-01-11 1979-07-25 THE PROCTER & GAMBLE COMPANY Composition containing a photoactivator for improved washing and bleaching of fabrics
EP0003371A1 (en) * 1978-01-11 1979-08-08 THE PROCTER & GAMBLE COMPANY Composition containing a cationic substance and a photoactivator for improved washing and bleaching of fabrics
US4166718A (en) * 1977-03-25 1979-09-04 Ciba-Geigy Corporation Process for bleaching textiles
US4217105A (en) * 1977-03-28 1980-08-12 The Procter & Gamble Company Photoactivated bleach-compositions and processes
US4240920A (en) * 1978-02-28 1980-12-23 The Procter & Gamble Company Detergent bleach composition and process
EP0035470A1 (de) * 1980-02-29 1981-09-09 Ciba-Geigy Ag Textilbehandlungsmittel
US4318883A (en) * 1977-03-25 1982-03-09 Ciba-Geigy Corporation Process for combating micro-organisms, and novel phthalocyanine compounds
US4400173A (en) * 1980-12-22 1983-08-23 Lever Brothers Company Bleach composition containing weakly to non-colored porphine photo-activator

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1372035A (en) * 1971-05-12 1974-10-30 Procter & Gamble Ltd Bleaching process
US3927967A (en) * 1972-06-02 1975-12-23 Procter & Gamble Photoactivated bleaching process and composition
US4033718A (en) * 1973-11-27 1977-07-05 The Procter & Gamble Company Photoactivated bleaching process
US4094806A (en) * 1975-04-03 1978-06-13 The Procter & Gamble Company Photoactivated bleach-compositions
US4077768A (en) * 1975-06-20 1978-03-07 The Procter & Gamble Company Inhibiting dye transfer in washing or bleaching
US4318883A (en) * 1977-03-25 1982-03-09 Ciba-Geigy Corporation Process for combating micro-organisms, and novel phthalocyanine compounds
US4166718A (en) * 1977-03-25 1979-09-04 Ciba-Geigy Corporation Process for bleaching textiles
US4217105A (en) * 1977-03-28 1980-08-12 The Procter & Gamble Company Photoactivated bleach-compositions and processes
EP0003371A1 (en) * 1978-01-11 1979-08-08 THE PROCTER & GAMBLE COMPANY Composition containing a cationic substance and a photoactivator for improved washing and bleaching of fabrics
EP0003149A2 (en) * 1978-01-11 1979-07-25 THE PROCTER & GAMBLE COMPANY Composition containing a photoactivator for improved washing and bleaching of fabrics
US4240920A (en) * 1978-02-28 1980-12-23 The Procter & Gamble Company Detergent bleach composition and process
EP0035470A1 (de) * 1980-02-29 1981-09-09 Ciba-Geigy Ag Textilbehandlungsmittel
US4400173A (en) * 1980-12-22 1983-08-23 Lever Brothers Company Bleach composition containing weakly to non-colored porphine photo-activator

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3729474A1 (de) * 1986-09-08 1988-03-10 Colgate Palmolive Co Zusammensetzung zum behandeln und reinigen von textilien
US5972038A (en) * 1994-08-30 1999-10-26 The Procter & Gamble Company Chelant enhanced photobleaching
US6413924B2 (en) * 1997-01-24 2002-07-02 Case Western Reserve University Photobleaching compositions comprising mixed metallocyanines
US8568991B2 (en) 2011-12-23 2013-10-29 General Electric Company Photoactivated chemical bleaching of dyes
US9176032B2 (en) 2011-12-23 2015-11-03 General Electric Company Methods of analyzing an H and E stained biological sample
US9250245B2 (en) 2011-12-23 2016-02-02 General Electric Company Photoactivated chemical bleaching of dyes
US9915592B2 (en) 2013-03-06 2018-03-13 General Electric Company Methods of analyzing an H and E stained biological sample
JP2017506272A (ja) * 2014-01-24 2017-03-02 ザ プロクター アンド ギャンブル カンパニー 表面を処理するためのシステム及び方法
US9834740B2 (en) 2014-01-24 2017-12-05 The Procter & Gamble Company Photoactivators
US9464375B2 (en) 2014-01-24 2016-10-11 The Procter & Gamble Company Kit for treating a substrate
US10098519B2 (en) 2014-01-24 2018-10-16 The Procter & Gamble Company Lighted dispenser
US10111574B2 (en) 2014-01-24 2018-10-30 The Procter & Gamble Company Method for treating dishware
US12139840B2 (en) 2018-06-11 2024-11-12 The Procter & Gamble Company Photoactivating device for washing machine

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GB8304384D0 (en) 1983-03-23
PT76256B (en) 1986-07-14
GR78065B (en)) 1984-09-26
IN156753B (en)) 1985-10-26
ES8407133A1 (es) 1984-08-16
ES519881A0 (es) 1984-08-16
CA1202452A (en) 1986-04-01
BR8300801A (pt) 1983-11-16
MY8700476A (en) 1987-12-31
EP0087833A1 (en) 1983-09-07
DE3364300D1 (en) 1986-08-07
AU544554B2 (en) 1985-06-06
PT76256A (en) 1983-03-01
GB2115027B (en) 1986-04-09
NO830577L (no) 1983-08-22
AU1143383A (en) 1983-08-25
EP0087833B1 (en) 1986-07-02
GB2115027A (en) 1983-09-01

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